Ethyl Acetate → 2-benzyloxy-N-methyl-N-(3-methyl-2-oxobutyl)acetamide

HRID 1416009Notes

Reaction equation

[CH3:1][CH:2]([CH3:8])[C:3](=[O:7])[CH2:4][NH:5][CH3:6].C(OCC)(=O)C.C(=O)([O-])O.[Na+].[CH2:20]([O:27][CH2:28][C:29](Cl)=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[CH2:20]([O:27][CH2:28][C:29]([N:5]([CH3:6])[CH2:4][C:3](=[O:7])[CH:2]([CH3:8])[CH3:1])=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 6.1 g (52.9 mmol)of 3-methyl-1-methylamino-2-butanone, 70.0 ml of ethyl acetate and 41.0 ml of water was stirred at 0° C. Added was 7.1 g (84.6 mmol)of sodium hydrogen carbonate, and the mixture was stirred for 10 minutes. There was added 8.5 ml (54.0 mmol)of benzyloxyacetylchloride over 30 minutes. After stirring at room temperature for 10 hours, the ethyl acetate layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel chromatography (hexane/ethyl acetate 1:1)to give 5.8 g of 2-benzyloxy-N-methyl-N-(3-methyl-2-oxobutyl)-acetamide (18a')(yield 42%).

Workup

additionAdded
stirringthe mixture was stirred for 10 minutes
stirringAfter stirring at room temperature for 10 hours
customthe ethyl acetate layer was separated
washwashed with saturated brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by silica gel chromatography (hexane/ethyl acetate 1:1)to

Sources & evidence

ORD record: ord-a52f0c1108394d338fab55d27c4518d0
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05910506

Reaction notes

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